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“Lethal Synthesis” of Fluorocitrate by Citrate Synthase Explained through QM/MM Modeling
Author(s) -
van der Kamp Marc W.,
McGeagh John D.,
Mulholland Adrian J.
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201103260
Subject(s) - citrate synthase , chemistry , aconitase , enzyme , citric acid , enantiomer , citric acid cycle , stereospecificity , stereochemistry , ab initio , biochemistry , catalysis , organic chemistry
A classic example of enzyme stereospecificity is the title reaction involving the enantioselective conversion of fluoroacetyl‐CoA. High‐level modeling of the enzyme reaction shows that preferential formation of an E‐ enolate explains the experimentally observed specificity. The results indicate that selectivity is primarily a result of the inherent energy difference between the E‐ and Z ‐enolates of fluoroacetyl‐CoA.